Hi, Leah. I'm a mother of four sons ages 12, 5, 2, and 15 months. I have to agree with the Nuby Sippy cups. I used those cups for my last two sons. They were both off the bottle at 12 months. They are similar to the format of a bottle. The suction part is soft like a nipple of a bottle. I think that is what made it easier for my kids to convert. I had no problems. Of course my little one cried a little, but he eventually got over it. I think he realized if he wanted something to drink he'd have to drink from the cup. My baby is 15 months and he already wants to drink from a regular cup. I think he wants to be a big boy like his brothers. He sees everybody drinking from regular cups and he grabs for a cup. He even gets excited when I set out the cups at lunch or dinner. He knows he's about to get his cup.
Just be tough and stick to your guns. You'll get it. But don't stress yourself too much about it. It'll be fine.